The New Assistant
by sushigreen
Summary: Damon Salvatore's new assistant, Elena Gilbert is a breath of fresh air in the high life that he currently lives with his girlfriend, Katherine Pierce. Katherine grows increasingly bitter as Elena and Damon grow closer than ever. Katherine starts messing with Elena's work, sabotaging, and attacking until Damon decides that it's time to intervene.
1. Chapter 1

"That comes out to twenty-three dollars, sir." The old man said as he handed Damon Salvatore the potted purple orchid plant. As the CEO of Salvatore Corp. his schedule was hectic and meetings were tight. For the past 3 years, his assistant Nancy had kept up all his meetings, lunch dates, due dates and everything imaginable. Unfortunately, Nancy was moving in with her long-time boyfriend, which meant she was leaving New York City and settling down in California.

"Thank you. I know my assistant would appreciate this plant much more than a bouquet. Here, keep the change." Damon handed the man a fifty and stepped out onto the already busy sidewalk. He appreciated Nancy; she managed not only to take care of Damon but his high maintenance girlfriend Katherine as well. As Creative Director of Eva Magazine she had her own personal assistant, but apparently her schedule was so busy that she needed to use his assistant on the weekends and sometimes weekdays too. He had no idea where he was going to find another assistant that would be able to take on both his and Katherine's schedule and not go insane. Fortunately, Nancy had agreed to host interviews even on her last day.

Standing in the back of the elevator, he couldn't help but look at the girl fidgeting in front of him. The constant shaking kept brushing into the orchids, even shaking some of the moss loose. He took a deep breath before looking back up to see how long until they reached the 25th floor. By the time the elevator stopped at the 20th, only him and the girl remained in the elevator.

Elena was nervous. After leaving college for more than three years, the only job that she had managed to land was a receptionist at a Toyota car dealership. It wasn't even full time. The student loans on her back kept looming over her but there was pretty much nothing she could do about it until she found a real full time job. Elena lived with her brother Jeremy and their aunt, Jenna. Jenna was providing for them now, and even helping Elena slowly paying back some of her college loans. However, Elena knew that sooner or later she was going to have to find a real job on her own and pay back Jenna. She had been online at websites looking for a job, when she stumbled on a posting from a woman named Nancy Gray about being a personal assistant to CEO. Why they didn't just promote people internally she'll never know, but she was grateful to have the opportunity, especially when Nancy had called back and confirmed an interview. That was how she had come to find herself standing inside an elegant elevator, fumbling with her folder, her purse, and her jacket.

When the doors opened, it was everything like she would imagine it would be. Everything was sleek, people were briskly walking, sending folders, notes and coffee to God knows where. Elena cautiously stepped in front on the receptionist's desk. The platinum blonde turned to her and smiled. "Hello, welcome to Salvatore Corporation. My name is Kristi. What can I do for you today?" Elena smiled and pulled out her iPhone to look at her email.

"Hi, I have an interview with Nancy Gray today at 10:30?"

"Of course, she mentioned that. Here," she pointed at the clipboard "Just sign your name on our visitor's log and I'll let her know that you're here." Elena took the clipboard and sat down on the sleek black leather couches in the waiting area. Elena sat down next to a pretty blonde who was on her phone playing solitaire.

After bringing the clipboard back to Kristi, she took the time to sit back down and look at what was hopefully her new workplace. The office was beautiful, looking like something out of Ugly Betty. Contrary to her belief, the people here weren't dressed in boring work clothes at all. Everyone was fashionable, every woman had heels on, and every man had a spiffy tie on. She looked down at her outfit. She had the slacks she was wearing since her freshman year of college. The blouse she had on was borrowed from Jenna, and her hair was in a simple pony tail. She sighed. She tried to put on a great interview outfit, but with her personal funds so tight right now, she had to work around things to make it work.

"Elena, Justin, and Emily?" A tall, brunette woman stepped in front of the waiting area and looked at Elena and two other people sitting on the couches. Elena followed the other two people into a large conference room and sat down to the left of the two. Nancy pulled herself a chair in front of the three interviewees and smiled.

"So, you're all interested in the position that I'm currently in. I'm moving to another state in a couple of days so I need to make sure that there's someone who will be able to do my job efficiently." She glanced down at her notes and flipped through the three resumes. "So, Justin, tell me about yourself." While Justin did just that, Elena's heart was thumping out of her chest while she thought about a good answer to that question. "Emily, how do you think you'll be able to handle a schedule that sometimes has hectic hours depending on the weeks?"

Crap. The questions were changing on her. Elena turned to look at Emily, who was sweating slightly and turned back to Nancy, who still had a big smile on her face, and nodding to Emily's answers. Nancy finally turned to Elena and flipped to her resume.

"I see that you've had some experience in administrative duties, do you think that you'll be able to change your work methods to fit an assistant rather than a receptionist?"

"Well that's an excellent question. I believe that I have the basics down for administrative duties. I'm prompt and I'm organized. In addition to keeping Mr. Salvatore organized, I'm willing to learn the additional duties of being Mr. Salvatore's assistant. "

"Great. I think I've got what I need for now. Thank you all for coming in, I'll contact you if you've got the job within the next three days. There's a break room right across the hall if any of you would like coffee or donuts."

Elena smiled, shook Nancy's hand and left. She knew she wouldn't be able to breathe until she left the building and got some fresh air. The interview was over, it was simple enough and she couldn't wait to get home to her family.

Damon placed the potted plant on Nancy's desk after she came back to her desk in front of his office after the interviews.

"Well, well, well. Damon Salvatore and plants? Who knew?" Damon turned and smiled.

"Well, for the most excellent assistant in the world, it's barely anything at all. I want to do more. So how'd the interviews go?" Nancy smiled and ruffled through the resumes and handed one to Damon.

"Her. She's sweet. She's fresh, and I feel like that girl seriously needs a break too. You should have seen how nervous she was in that room, but I think I spy some inner confidence in her." Damon looked at the resume and flipped to the next page to see a picture of the girl. It was the girl in the elevator. She seemed sweet enough. Her straight brunette hair framed her heart shaped face. Her makeup was simple yet beautiful. The straight shot of her face gave Damon the feeling that this was a woman on a mission.

"She seems great. She kind of looks likes Katherine too actually." Nancy pulled the resume to look at it again.

"Wow, she does. Didn't really notice, but the two of them are like night and day. You know that Katherine would never wear a plain blouse from someplace like Forever 21."

"Which is terrible for me, because being the gentleman, I gotta pay for her stuff whenever I shop with her. I love her though, I'll give her anything." Nancy smiled.

"I'm actually surprised that you guys have lasted so long. Katherine seems to really make you happy, but I'm surprised at how sometimes she's so jealous. Remember that time she thought that we were together even though my boyfriend proposed?" Damon laughed and put his hand over his eyes.

"I don't even want to remember that. It was ridiculous."

"I bet she's glad that I'm leaving. She won't have to think that we're cheating on her." Damon rolled his eyes.

"Seriously though, Nancy, I really want you to know that I appreciate all the things that you have done for me. Taking care of me must have not been easy and you've been here with me since the day that I started. You've been a great friend to both my brother and me. And thanks for finding me a new assistant too. She seems like a sweetheart. Do you think she'll be able to handle it?"

Nancy looked up from the email that she was sending to Elena. "Well, I know that she'll be able to handle you. She might even give you a taste of real life outside of the Upper East Side, but with Katherine, I'm going to assume she's going to be a little troubled. I'm sure that she'll get over it though. I sure did."

Damon's cell phone rang in his office. "I sure hope so." He went in, and picked up. Breaking in a new assistant was going to be tough, but maybe she'll be a taste of fresh air. Newbies always are.


	2. Chapter 2

Elena stood outside of Damon's office. It was her first day at work and she was finally going to meet her boss. She took a deep breath and knocked.

"Come in." Elena stepped inside and shut the door. This was the first time she was going to see him in person. As soon as she got the email from Nancy, she looked up everything that she could on Damon Salvatore and the company. He had a brother, Stefan Salvatore, and his girlfriend was Katherine Pierce, the creative director of Eva magazine. He looked hot in the photos, but she wasn't expecting the difference in real life. The man was gorgeous. His chiseled features were sharp and his eyes seemed like they could look into her. The man in front of her smirked.

"Well, if you aren't my new assistant, Elena Gilbert. I must admit, you're more gorgeous in person." He circled her. Elena felt like she was being circled like a hawk. It was almost like she could sense the danger playboy in him.

Damon watched her reaction. She was a petite, cute little thing. She looked so innocent, it was a little disconcerting. Her long brunette hair framed her heart shaped face perfectly, drawing him to her plump peach lips. Her collarbone was tantalizing. He was with Katherine, he knew that, but he also knew what kind of person he and Katherine both were. They were both out to play the game, Katherine tended to manipulate people more so than he did, he was just having fun. He never tried anything with Nancy, because they had pretty much grew up together. Even to someone like him, people like Nancy and Caroline Forbes were off limit. Getting with a childhood friend was just wrong, and so was getting with his brother's girlfriend.

"You're a cutie. Do you think you'll be able to handle Nancy's job? It's a difficult one. You're going to have to assist me pretty much night and day…" he gave her a smoulder.

"I think I'm ready." Damon handed her a book the size of a 5-subject notebook.

"This is my appointment book. All of the things that I need to get done on a daily basis are here. I need you to make sure that I'm reminded of each of these things. I like to be reminded of my events that I need to get to an hour before I need to leave. Would you like to have lunch with me today? I'd like to get to know my beautiful assistant better." Elena forced a smile. She didn't want to upset him on the first day. She nodded. "Great, I'll have the car pick us up at twelve. In the meantime, can you get this memo over to Stefan's assistant Bonnie?" He handed her a blue file folder.

Elena took the folder and began walking down the hall. She knew he was hot, but she had assumed off the bat that he was the type of person that would be faithful to Katherine, but from what she just experienced it seemed like he had no problem flirting up a storm with other women. What kind of person did that make him if he couldn't be faithful?

In front of Stefan's office was Bonnie's desk. Bonnie was a sweetheart, she offered to show Elena around, get her used to the way that the two brothers ran the corporation.

"I know you're Damon's assistant, and the temptation will be super intense, but it would be safer for you if you didn't get too involved in Damon's personal life. His a little dangerous when it comes to the ladies. I know he's hot and everything, but I've seen the girls that he flirts with and they always end up getting too involved, you know?" Elena nodded, completely understanding what she meant.

"I sensed something when I met him just then. He's a flirt, but I thought he was with Katherine?" Bonnie nodded.

"He is, it's just that, apart from tons of flirting, he doesn't necessarily cheat on Katherine. It also helps actually that they're both that type of person because Katherine does it as well. From what I hear anyways, I wouldn't know since I obviously don't really see her that much, what with being Stefan's assistant and all. You would think that Stefan and Katherine talk a lot, but they really don't. I really think Stefan goes out of the way to avoid Katherine unless he really needs to reach her." Elena smiled.

"Sure seems like she's a dangerous woman. I hope I don't ever end up crossing her." Bonnie shook her head.

"I'm actually sure that you will, and even if she'll never get over it, you'll be able to handle it because you'll get used to it. Nancy did, I'm sure." Elena nodded.

"Well, I gotta get back. I need to answer some emails before lunch. The office was already bustling with people even at eleven in the morning. People kept staring at her as she walked past their little cubicles, probably trying to see what type of assistant she was.

Damon saw Elena come back around the corner before sitting down back at her desk and began working on her computer. For a girl with such a hot body, she sure seemed like the innocent type. Her conservative blouse and her long slacks provided more than enough cover up. Nancy knew what he was like. She would give him advice on the women that he flirted with, advice on his relationship with Katherine, and advice on pretty much everything else. Elena on the other hand was pretty much a complete stranger. He had no idea if she was stuck up, or quiet, or outspoken, or anything really. Maybe he'll get to figure her out a little bit over lunch. Work was slow today, not one of the busier ones, he send a couple emails, read a couple files, and signed some documents before his cell phone rang again.

"Hey Kat"

"Damon, how's the new assistant looking?" Damon shrugged as he continued staring at Elena's back through the opaque glass.

"She's doing her job, not slacking off, but it's her first day, so we won't really know."

"Damon…you know that's not what I meant."

"She's pretty."

"I don't want you flirting with her or anything, at least until I've met her and decided if I hate her or not." Damon rubbed his eyes. Katherine and he had such a weird and pretty much unstable relationship. She seemed to almost like it when he flirted with other people, not that he minded of course. He like Katherine, he really did. Sometimes, it just got overbearing when she played her mind games. It was almost like a cat and mouse, hard to tell sometimes just who was which.

"Katherine, you're going to be nice to her if you meet her. She seems like the innocent type, and I doubt she's going to do anything okay?"

"Why are you already defending her? All I said what that I wanted to meet your new personal assistant. Why do you always just simply assume that I'm going to do something terrible or that I'm going to ruin whatever relationship that you guys have going on?"

"Woah. Katherine, seriously, I'm not in the mood for an argument right now, okay? It's way too early for this shit. We don't have a relationship. I'm her boss, she's my assistant. That's it."

"Alright. Want to have lunch today?"

"I'm having lunch with Elena, my assistant? Today is her first day, so I want to get to know her better."

"Great, sounds good. Where should I meet up with you guys? Twelve, right?" Damon shook his head. It was things like this that got him tired sometimes of telling Katherine about plans that involved any other girl that she hadn't already met and decided that she didn't need to worry about.

"No, Kat. It's her first day, and I think having lunch with the both of us will make her a third wheel and make it more difficult for her. I'm sure she's nervous enough on her first day."

"I'm not going to do anything to her, my God!"

"Katherine, you and I both know that our relationship is nothing like the relationships that I'm sure normal people actually have."

"Please, babe. You know you love it." Katherine hung up. Damon sighed and put his head into his hands. He had met Katherine a while back. At the time, he had to admit that it really was a whirlwind romance, but lately he was starting to get tired of her constant need for drama. He wished that Katherine could be genuine just once in a while. Instead of mind games, secret meaning and such all the time, he wondered what it would be like to be with a girl who was honest, genuine, and real. He wanted someone who had no desire or need to hide anything.

Damon looked up at the wall clock. Time for lunch.


	3. Chapter 3

"I'll have a baked ziti, no garlic please." Elena handed the waiter the menu and smiled. The waiter turned to Damon.

"I'll have what she's having." The waiter took his menu and walked away while Elena fidgeted in her seat. She thought that she'd be excited to get to know her new boss, but that was before she met him and had that encounter with him in his office. Damon was peering at her with his chin propped up with his fingers.

"So, how has your first day been going so far?" Elena shrugged.

"Pretty good so far, I mean, people at the office are really nice and things have been going quite smoothly with your appointment bookings and such." Damon nodded.

"How about other than work? How's work going so far?" Elena gave him a puzzled expression.

"You're asking me how work is but you don't want me to talk about work?" Damon chuckled.

"What do you think about me? Hot, right?" Elena scoffed.

"Wow, cocky much?" Damon placed his hand over his heart and feigned being hurt.

"Now now, Elena. Is that anyway to talk to your new boss? After all, I'm the one writing your checks right?" Elena uncrossed her arms from her chest and placed them squarely on the table and stared at him. Elena was getting angrier by the minute, did Damon need a new assistant to work for him or did he just need someone else to sleep with?

"Damon, let's get this clear, I'm your personal assistant, I do work for you that's related to the company. Nothing more." Damon shook his head.

"You know, actually that's not quite true. You're not just an assistant, you're a personal assistant, meaning when I need something, someone helps me do it, that someone being you." He smirked. He placed his hand over hers. Elena glanced down at their touching hands, she felt her heart beating a little faster, however, from what, she didn't really know. She couldn't tell if it was being the frustration was building up to the tipping point, or if she felt a strange shudder go through her.

"Get that hand off of that whore!" Elena and Damon instantly turned around to look for where the voice came from, as well as the several tables that they were next to. Elena quickly withdrew her hand and placed them under her thighs and kept her eyes on the woman that seemingly came out of nowhere. Damon slowly retracted his hand from the table and soothed out wrinkles he was developing on his forehead.

"Katherine, this is ridiculous." So this was Katherine, Elena took in Katherine's appearance and to say she was impressed would have been an understatement. Katherine was wearing high black stiletto shoes, tight black dress, and a string of pearl necklaces. With her cleavage popping, her hair in a high straight, long ponytail and diamond studs, she looked like a woman not to be messed with. Damon stood up and pulled a chair to his left for Katherine. "Katherine, this is Elena, she's going to be replacing Nancy as my personal assistant, remember? Today is her first day, I'm just having lunch with her today to get to know her a little better."

"Is that so…" Elena didn't move from her seat, and now she suddenly found her empty plate in front of her extremely interesting as Katherine continued staring at her.

Katherine was used to the jealous game with Damon, after all, he was a very handsome guy, but this girl irked her just a little too much for her comfort. She was so many similarities between herself and Elena. Of course, Elena was nothing like her if you compared them now, Katherine was a highly respected creative director, but back in her early days right after her graduation from college, Elena reminded Katherine of herself; of herself back in the day when her and Damon first met each other and fell in love. Perhaps, the way to deal with her was not to be ruthless up front. Damon seemed to have taken a liking to this girl; Katherine knew that it would cause trouble if she was rude for no apparent reason.

"I'm so sorry, Elena. I jumped to a conclusion when I saw you two together. It's nice to meet you." Elena looked up as soon as Katherine started to talk to her. Katherine smiled at her, showing her row of perfectly shaped, pearly whites. Her smile didn't reach her eyes. As soon as Elena reached her eyes, she flinched. She suddenly felt like a helpless prey and Katherine was getting ready to swoop in. Elena panicked. She definitely didn't want to quit this job, seeing as how hard it was to land it in the first place, but was she really ready to take on Damon Salvatore and Katherine Pierce? Damon was this cocky and dangerous man while Katherine was getting ready to eat her alive. How long was she going to last in their game? For a couple living the life, they certainly have their fair share of issues.

"It's fine. It's very nice to meet you." Katherine continued her fake smiling. "I actually think I'm been out for too long, assistants don't get such long breaks. " Elena stood to get up. Damon waved for her to sit down.

"Elena, you're out to lunch with me, besides, your food hasn't even come yet." Katherine turned to give Damon a strong piercing look.

"Elena, if you're busy, you should go ahead and head back to work, I've been meaning to have lunch with Damon anyway." Elena smiled and stood up.

"I'll see you back at the office," she said to Damon, "and it was really nice to meet you, Katherine." Katherine nodded and watched Elena head out the door. Katherine stood up and sat down in the seat Elena was previously in.

"Seems like a nice girl." Damon nodded.

"Which is why you really didn't have to scare her like that, Katherine." Katherine shrugged,

"I'm just protective of my man, that's all. Why was your hand on top of hers again?" Damon smirked. He put his hand on Katherine's like he did to Elena's and leaned over and kissed her on the lips.

"Oh, babe, just some harmless flirting, nothing serious of course." Katherine raised an eyebrow before pulling out her blackberry. Damon stared at her. "Katherine, if you're not even going to look at or talk to me, why did you make Elena leave? At least she was actually talking to me." Katherine slowly put her phone down.

"Sorry honey, I was just setting up my lunch date with Mason for tomorrow." Damon frowned.

"Mason? Why are you having lunch with Mason? I know it's not about business." Katherine shrugged.

"You're right, it's not about business. I just haven't seen him in a while and when he decided to hit me up, I decided to accept? Something wrong with having lunch with someone?"

"There's something wrong when you tell your present boyfriend that you're going to have lunch with your ex and flaunt it in front of me." Damon paused as the waiter came and set down their food.

"Baked ziti? You hate baked ziti, why would you get something like this?" Katherine said as she watched Damon dig in.

"I just think I needed a change." Katherine sneered.

"And it just so happens that you and Elena were about to eat the exact same meal?"

"Don't try to change the subject, Katherine. Why are you having lunch with Mason? He's your ex, I'm not okay with you being alone with him." Katherine smirked and a second later, he felt Katherine's bare food moving slowly up his leg.

"Does it make you that angry that I'm hanging out with Mason? Does it make you feel possessive? Does it scare you, Mr. playing the field?" Katherine knew she won as Damon waved the waited by to get their food packed up and pay the bill.

Elena glanced at the wall clock to her right. It was three and Damon still wasn't back from lunch yet. Damon had a phone conference that he had to get on at 3:30 sharp. Elena tapped her fingers on the phone before deciding it was more important to get her job done that disturbing Damon. She punched in his numbers and waited as it rang.

"Hello?" a sleepy voice answered. Elena frowned, was Damon really sleeping in the middle of the day? What kind of CEO did things like that? From her desk she could see Stefan' shadow in his office hard at work.

"Is this Damon?"

"Yes, who's this?"

"Elena? Your assistant. You haven't come back from your lunch yet, and you have a phone conference you have to get to at 3:30, that's in half an hour." In the background, Elena heard a voice calling.

"Come back to bed, honey, ready for round three?" Elena shuddered. So he was having a little afternoon delight with his girlfriend. How he managed to run a company, she really had no idea.

"Ok, sorry about that Elena, could you just send me their number and email me the outline? I'll make the call from my penthouse. Thanks." Before Elena could say another word, he had already hung up.

Elena sighed, she knew going into the job that working for Damon was going to be a difficult task, she just failed to realize just how hard it was going to be in terms of patience and trying to keep herself from judging him.

Damon sat down on the edge of his bed and turned to look at Katherine sprawled out naked on the bed.

"You knew that was Elena, why did you do that?" Katherine frowned.

"Honey, I was just trying to ask you a question, I didn't mean for her to hear or anything? What are you so worried about anyway? Why does she matter so much? She's just an assistant and today is her first day." Katherine pulled him back and laid him out on the bed.

"Katherine, just get back to work, I've had enough for one day."


	4. Chapter 4

Elena paused before knocking on Damon's office door the next morning. Hesitantly, she lifted her arm when Damon pulled the door open. Blue met brown. Elena gave him a small smile and handed him the Starbucks he wanted.

"Good morning Damon, I have your morning briefing ready. You have no appointments this morning, but HR wants the 'letter from the CEO' by 11am and you haven't started that yet. Then in the afternoon, you have lunch with Stefan and a meeting with the recruitment department. I'll have your presentation sent to your email in just a minute." The second Elena paused to take a breath, Damon jumped in.

"I'm sorry about yesterday, Elena. It was out of line for Katherine to do that to you." Elena smiled and shrugged her shoulders.

"Really, it's totally fine, I understand where she's coming from. Also, she didn't really do anything to me." Damon studied her face, she acted like she was okay, but he could tell the events of yesterday were still bothering her. Damon placed the cup of coffee on her table before closing the distance between them and giving her a hug. Elena's eyes widened from the sudden closeness. She didn't know how to react as the scent of his cologne filled her senses. She slowly returned the hug, wrapping her arms around his waist as his arms circled her shoulders.

"I shouldn't have let her done that to you," Damon whispered in her ear. Elena sighed. She tried to pull back which only made him hold on to her tighter.

"Damon, I don't think is appropriate. You're my boss and you have a girlfriend and…" Damon pulled away slightly to get a front look of her face. His face was serious for a moment before returning to that smug face he always wore.

"Don't say you don't like it, because I know you do." Elena rolled her eyes before finally pushing him away. "By the way, you forgot that the Lockwood benefit dinner is tonight, I need my suit dry cleaned and pressed before 5 pm, after which you will accompany me to the dinner." Elena's head instantly turned at that.

"What do you mean; I'm accompanying you to the dinner? I'm your personal assistant. Isn't it Katherine's job to be your date?" Damon just shrugged and turned back towards his office.

"She's busy tonight, something about the new issue coming out and a screw up on the how to section of the magazine. Anyways, if we're going to forever be professional here, shouldn't you just have said 'yes, Mr. Salvatore.'"? Elena resisted the urge to roll her eyes again.

"Yes, Mr. Salvatore. I'll be ready." Damon chuckled and tisked with his tongue.

"No dirty talk in the office, Ms. Gilbert."

Elena spent the rest of the day reminding Damon of his letter to HR until lunch. The only moment she was able to take a break was spent riding Damon's car to his penthouse to grab his favorite suit for dry cleaning. Stepping out of the vehicle, she approached the friendly doorman ready to open the door for her.

"Hello miss, I've never seen you around before, do you have an entrance permit perhaps?" Elena smiled and reached into her purse, taking out the key card Damon had given her earlier. "Ah, Mr. Salvatore's penthouse, I'm surprised you got past the Mrs." Elena raised her eyebrows curiously. Damon was married? "Well, they're not married, but Ms. Katherine Pierce spends a fair share of her time here. In fact, the other doorman told me she was here a while ago, but," he checked his watch "we changed shifts, and she must have left by now, it's been hours." Elena felt a weight she didn't know she had lifted off her shoulders. The last thing she needed was to run into Katherine, but wasn't Katherine supposed to be working on the latest issue of Eva?

Elena headed over to the specially marked elevator at the end of the long hall in the lobby labeled specifically for the penthouse suite. The door opened to a large room with a beautiful painting on the opposite wall. Taking a couple steps forward, she could either go to the left or to the right. The left led to a hallway with five open doors. The right led to three large walkways to what Elena presumed to be the living room, dining room, and kitchen. Elena placed her purse on the low black leather bench by the wall and headed to the left. Peeking into the first room which turned out to be the restroom, she was that the style of his office seemed to apply to his house as well. She passed the second door, when she looked in and saw a small office. The third room was larger than the first two, with what seemed like a zen room. There was a large bamboo plant on the glass table on the far wall. There was a huge bean bag bed in the other corner with a large plasma tv opposite of it. The right wall had been reconstructed to create an ongoing waterfall lined with a blue LED light. If Elena had the time, she would definitely crash in this room. The next room was a guest bedroom with a door connecting to the next room. Elena walked into the final room. The large room had a door connecting to the guestroom in one room across from a large king sized bed decked with light gray bed sheets neatly made. The room also contained a small door to a walk in closet, a bathroom, and another television. Elena made a beeline for the walk in closet, the door slowly closing behind her. Elena couldn't believe what she was looking at. The countless wall of suits, the row of identical black leather shoes, the floor to ceiling organizer with various ties of all colors and designs. Elena shifted through the rack of suits to find the right suit. Black Armani with silver lining…Black Armani with silver lining…Black Armani with silver lining…BANG

Elena turned to look at the closed closet door leading to Damon's bedroom. Was somebody breaking into Damon's penthouse? Katherine was at work, Damon was definitely back at the office, but security was so tight here, who would it be? Her eyes darted around the room to look for something hard she could use as a weapon if the person was an intruder…that was when she heard Katherine's voice.

"Do you have it?" Elena recognized her voice. It was smooth, determined, and just a little dangerous.

"Damon's favorite wine, he'll be wrapped around your finger in no time. Why do you even want him so much? I mean, you flirt with everything that walks, why him?" An unknown male voice answered.

"I've known Damon for a long time now, he's the only constant thing in my life, and I'm going to be damned if I let him be snatched up just because I'm too busy to keep tabs on him lately." Elena held in her breath. For a crazy, flirtatious bitch, she was extremely jealous over somebody she treated like shit. Elena turned her head when she heard Katherine speak again. "I gain people's respect through my job, I gain money based on a moderate salary and my excellent choice in stocks. I invest in Google, Boeing and especially Apple, but most of all, I invest in Damon." She heard some pounding, footsteps, and the front door close down the hall before opening the closet door. Life as Damon's personal assistant was getting more and more dramatic….and then there was the Lockwood benefit dinner.


	5. Chapter 5

Elena hung Damon's dry cleaned suit on the coat rack in the corner of his office. He was still with the recruitment department on the twelfth floor. She checked her watch, it was already 4:30 and he still wasn't back. Elena glanced out the office window as if he would just appear outside. Although employees were supposed to leave at 6pm every evening, a lot of them would start skipping out at 5; people were already packing to leave on the dot. Elena sighed, for the past couple of days she would be too, but seeing as how she was going to accompany Damon to the Lockwood benefit dinner, she might as well kill some time. It felt wrong to stay in his office while he wasn't there, so she turned around and sat down at her own small little desk. She drummed her fingers across the table top. All his meetings were scheduled, nobody was waiting on the call line, all her memos and emails were sent…there was nothing to do but sit…Elena let out a deep sigh and closed her eyes, leaning back in her ergonomic chair.

"Hope I'm not interrupting you," a voice woke up Elena some time later. Elena woke up startled. Damon Salvatore was standing in front of her desk carrying an iPad and a dark grey box. Elena shook her head and rubbed her eyes.

"I'm sorry; I was just resting my eyes for a moment. I have your suit dry cleaned and pressed, it's waiting in your office." She finally noticed that the office behind him was pretty much empty, the remaining people packing up and walking towards the elevators, glancing at the clock it read 5:54 pm. Damon smiled.

"It's good, after you're all rested up, you can be more ready for the benefit." Elena nodded. I called Mr. Donovan; the town car should be waiting for us soon. He'll text me as soon as he's ready." Damon nodded and gestured for her to follow him into his office. He closed the door slowly behind her. He strolls over to his desk and eyes the hanging suit as he placed his iPad on his desk.

"Elena, what are you wearing to the benefit?" Elena shrugged.

"What I'm wearing right now? I didn't know that you wanted me to change, and I don't have any time to go home now." Damon smiled and handed Elena the grey gift box. "This is for you, Elena. I need my assistant looking beautiful at the dinner, not that you aren't already extremely sexy." He gave her the irresistible smile. Elena felt herself blush as she opened the box. She gasped. She couldn't even see what the dress looked like yet because it was covered with tissue paper, but lying on top of the tissue paper was a very expensive looking black velvet box. Damon took the larger box from her and let her hold the black box. The top snapped open to reveal a gorgeous, elaborate diamond necklace. The necklace had diamonds all along the edge, the front decoration were various icicle diamond drops, the longest one being where her cleavage would be. Elena looked up, and was about to tell him how she couldn't possible wear this before Damon spoke. "Wear it, Elena. It'll look beautiful on you."

"I can't take this, it's far too expensive." Damon shook his head.

"I'm the CEO of a successful corporation, if you thought that this necklace cost a lot to me, you don't know me very well." Elena raised her eyebrows.

"I don't know you very well; I've only been working for you for a couple days. Beside the point, I just can't have this. Thank you, but no thank you." Damon took the box from her, and Elena sighed thinking she had won the argument. He took the necklace out of the box and approached her from behind. The closeness made Elena shudder. Damon was her boss, her brain knew that, her body however, knew he was gorgeous, he smelled good, and he was getting more and more irresistible.

He pushed her hair from her back so that it lay on her left shoulder. He placed a swift kiss on her shoulder, making Elena almost jump at the contact. He finished placing the necklace on her neck and turned her around.

"You look absolutely stunning, just like I knew you would." Elena's face, now as red as a tomato, looked down at her feet before shyly peeking up at him.

Damon looked at her smile; it was rare that he saw a genuine smile. As a corporate leader, he came into contact with so many people who faked their emotions either to get on his good side, or to land a contract with his company. Damon didn't have many friends, and the friends that he did had were all spoiled by their fathers, who named them CEO of their company, leaving their company in the hands of a clueless frat boy who would inevitably run it into the ground. He couldn't remember the last time he got the carefree feeling he got in college. Meeting people, meeting girls, trying new things, nothing to worry about but what time and where the next party would be. Elena reminded him of that young life, the life before taking on the heavy responsibility of the business. Elena looked so innocent. She reminded him of those girls he would never talk to because he knew they were frigid and he'd have no chance of getting laid with them. Maybe now was the time to try.

Damon leaned forward slowly, trying to test out Elena's proximity boundary. When she showed no response, he inched further. He was now so close to her, the sides of his suit grazed her blouse. Elena slowly lifted her head and stared into the endless blue eyes. She didn't even realize she was biting her own lip until she saw him biting his. He felt his heart beat so fast he thought it'd come right out of his chest. He couldn't think of anything but what he saw, and what he saw he wanted. So he took it.

He went in and kissed her. Elena was shocked but found herself unable to pull away. She involuntarily let out a soft moan and Damon took that opportunity to get in. He grasped the back of her neck and pulled her in closer, wrapping her tight in his hug. Elena found herself pulling on the back of his shoulders to get her a little lower to her height to deepen the kiss. Elena was so out of control of her body, she felt her knees get weak and give out from underneath her. Damon wrapped his arm around her waist just before they both fell back onto the black leather couch. Breathing heavily, Damon attacked her neck hungrily with kisses as Elena buried her face in his neck, deeply inhaling his addictive cologne. KNOCK KNOCK.

The knock on the door brought Elena back to her senses. She pushed Damon off of her and pulled her slipped off cardigan. Rubbing her nose nervously, Elena got up off the couch and soothed out her shirt. Damon adjusted his tie and cleared his throat. "Come in." Stefan leaned in with a smile on his face.

"Hey, you guys ready to go? Donovan is already here with the town car."

"And who said you could hitch a ride with us, little bro?" Damon smirked causing Stefan and Elena to both roll their eyes.

"Well, I'm your brother, and Matt Donovan is the family chauffer." Stefan said, emphasizing on the 'family'. Elena took her phone out of her pocket and found she missed the text from Matt saying the car was indeed here. "Elena, you're still in your work clothes? Did you hate the dress Damon picked out?" Stefan laughed, causing his brother to scowl.

"You interrupted her, she was just opening it. Check it out, Elena." Elena smiled and hesitantly walked over to the table where the box lay. Lifting the tissue paper off the dress, Elena's eyes and smiled widened. She took it out of the box, and the smooth, lacy material flowed to her feet. She couldn't tear her eyes away from the dress. The pitch black dress was an incredibly lace only plunge followed by the laced covered silk dress bottom that seemed to travel for miles.

"Damon…This dress is incredible." Damon smiled and ran his hand through his already messed up hair. He regretted getting her that dress now. The cloth plunge on the upper part of her body was ONLY lace; he was already dreading the night of getting a teased peak of her breasts. Elena smiled.

"Well, I'm going to put this beauty on; I'll be back in a second, boys." Stefan stepped aside and smiled. As soon as she was down the hall, he turned back to Damon.

"Are you sure you know what you're doing?" Damon looked up from unzipping the bag with his suit.

"What you mean, I'm smarter than you." Stefan rolled his eyes and crossed his arms.

"What kind of boss gives his assistant a dress like that? It must have been expensive." Damon sighed, taking the suit off the hanger.

"I know it may sound surprising, Stefan, but some people actually like to treat their personal assistants with some gifts so that they may be more cooperative and helpful in the future." Stefan scoffed.

"Yeah? Cooperative in what way?" Damon pretended he didn't hear him as he put on his cuff links. "You do remember this girl named Katherine Pierce right?" At that, Damon narrowed his eyes.

Truth was, Katherine was the last person on his mind right now. He wasn't afraid that Katherine would be mad because it was common for them to kiss other people, and the more he thought about it the angrier he got that Katherine rubbed the dinner with Mason in his face. Their only rule was that they don't sleep with other people, so technically he was still in the clear. Nothing wrong with it. He was scared Elena might be one of those girls who'd get under his skin; afraid that a fast lay might turn into something more, especially if they worked together… KNOCK

Stefan and Damon looked up to see Elena standing in the doorway.


End file.
